Upcoming Chicago Drag Shows

Drag meets Music City flair at City Winery Chicago. Live music, laughter, and vibrant performances make every show sparkle!

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City Winery Chicago celebrates the art of drag with shows that blend music, comedy, and dazzling performance. Each evening brings a lineup of talented entertainers who fill the room with energy, color, and heart. Between drag events, our venue also hosts rock, R&B, and comedy shows that keep the calendar full and lively. With fine wine, local cuisine, and a welcoming ambiance, every show is a celebration of creativity and community.


Plan Your Visit

Directions, Parking & Dining at City Winery Chicago

City Winery Chicago is located at 1200 W Randolph Street in Chicago’s Fulton Market District, one of the city’s most vibrant dining and entertainment neighborhoods. Whether you're coming for live music, a comedy show, or dinner and a show, getting here is easy.

Parking: Paid parking is available just two blocks away on 14th Street, along with additional garages and street parking throughout the surrounding West Loop neighborhood.

Public Transit: City Winery Chicago is easily accessible via public transportation. Take the B train to the 19th & Lake stop, which is just a short two-block walk from the venue.

Rideshare: Uber, Lyft, and other rideshare services frequently drop off and pick up guests directly in front of the venue, making it convenient to arrive or leave after a show.